NO115842B - - Google Patents
Info
- Publication number
- NO115842B NO115842B NO15123363A NO15123363A NO115842B NO 115842 B NO115842 B NO 115842B NO 15123363 A NO15123363 A NO 15123363A NO 15123363 A NO15123363 A NO 15123363A NO 115842 B NO115842 B NO 115842B
- Authority
- NO
- Norway
- Prior art keywords
- methoxymethyl
- group
- residue
- alkoxy
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000003277 amino group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- PXDBUWPMANSAFI-UHFFFAOYSA-N 4-amino-n-pyrimidin-4-ylbenzenesulfonamide Chemical class C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=NC=N1 PXDBUWPMANSAFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- -1 methoxy, ethoxy Chemical group 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- GETQZCLCWQTVFV-UHFFFAOYSA-N anhydrous trimethylamine Natural products CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 229940124530 sulfonamide Drugs 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- AUYLLSDPDMYNTF-UHFFFAOYSA-N 4-amino-N-[6-methoxy-2-(methoxymethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)OC AUYLLSDPDMYNTF-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 8
- 150000003456 sulfonamides Chemical class 0.000 description 8
- JEOBFTOIMFEXNK-UHFFFAOYSA-N 6-chloro-2-(methoxymethyl)pyrimidin-4-amine Chemical compound COCC1=NC(N)=CC(Cl)=N1 JEOBFTOIMFEXNK-UHFFFAOYSA-N 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- RVEGXZSTKXPVPB-UHFFFAOYSA-N S(=O)(=O)(O)Cl.C(=O)(OCC)NC1=CC=CC=C1 Chemical compound S(=O)(=O)(O)Cl.C(=O)(OCC)NC1=CC=CC=C1 RVEGXZSTKXPVPB-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- AUNQXUFJXZBTIV-UHFFFAOYSA-N 2-(methoxymethyl)pyrimidin-4-amine Chemical compound COCC1=NC=CC(N)=N1 AUNQXUFJXZBTIV-UHFFFAOYSA-N 0.000 description 4
- HUKHOBYZPBKOQG-UHFFFAOYSA-N 4-amino-N-[6-chloro-2-(methoxymethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)Cl HUKHOBYZPBKOQG-UHFFFAOYSA-N 0.000 description 4
- JHQXVCAOBDYYTL-UHFFFAOYSA-N 6-methoxy-2-(methoxymethyl)pyrimidin-4-amine Chemical compound COCC1=NC(N)=CC(OC)=N1 JHQXVCAOBDYYTL-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- VZTVSUKTMWSTOG-UHFFFAOYSA-N 2-(2-methoxyethyl)-6-methylpyrimidin-4-amine Chemical compound COCCC1=NC(C)=CC(N)=N1 VZTVSUKTMWSTOG-UHFFFAOYSA-N 0.000 description 3
- WTVXSDIYBZLDIN-UHFFFAOYSA-N 2-(ethoxymethyl)-6-methoxypyrimidin-4-amine Chemical compound C(C)OCC1=NC(=CC(=N1)OC)N WTVXSDIYBZLDIN-UHFFFAOYSA-N 0.000 description 3
- LRAIBXGPDUQUBD-UHFFFAOYSA-N 4-chloro-2-(methoxymethyl)-6-methylpyrimidine Chemical compound COCC1=NC(C)=CC(Cl)=N1 LRAIBXGPDUQUBD-UHFFFAOYSA-N 0.000 description 3
- QLPMACVIRPWEKZ-UHFFFAOYSA-N 4-chloro-6-(methoxymethyl)-2-methylpyrimidine Chemical compound COCC1=CC(Cl)=NC(C)=N1 QLPMACVIRPWEKZ-UHFFFAOYSA-N 0.000 description 3
- QOOQUMTZWQEHTR-UHFFFAOYSA-N 4-chloro-6-(methoxymethyl)pyrimidine Chemical compound COCC1=CC(Cl)=NC=N1 QOOQUMTZWQEHTR-UHFFFAOYSA-N 0.000 description 3
- KZCDPEWXWGDVKM-UHFFFAOYSA-N 6-ethoxy-2-(methoxymethyl)pyrimidin-4-amine Chemical compound CCOC1=CC(N)=NC(COC)=N1 KZCDPEWXWGDVKM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- KERKSHQWMCWPBT-UHFFFAOYSA-N n-phenylacetamide;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CC(=O)NC1=CC=CC=C1 KERKSHQWMCWPBT-UHFFFAOYSA-N 0.000 description 3
- 229940072033 potash Drugs 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XTAUZKNANNHWQL-UHFFFAOYSA-N 2-(methoxymethyl)-6-propan-2-yloxypyrimidin-4-amine Chemical compound COCC1=NC(=CC(=N1)OC(C)C)N XTAUZKNANNHWQL-UHFFFAOYSA-N 0.000 description 2
- JIQYMVXNVNFXIP-UHFFFAOYSA-N 2-methoxyethanimidamide;hydrochloride Chemical compound Cl.COCC(N)=N JIQYMVXNVNFXIP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- CSIFGMFVGDBOQC-UHFFFAOYSA-N 3-iminobutanenitrile Chemical compound CC(=N)CC#N CSIFGMFVGDBOQC-UHFFFAOYSA-N 0.000 description 2
- KRGDUBQLCSQJJK-UHFFFAOYSA-N 3-methoxypropanimidamide;hydrochloride Chemical compound Cl.COCCC(N)=N KRGDUBQLCSQJJK-UHFFFAOYSA-N 0.000 description 2
- JEGIGVNQAHMOII-UHFFFAOYSA-N 4,6-dichloro-2-(methoxymethyl)pyrimidine Chemical compound COCC1=NC(Cl)=CC(Cl)=N1 JEGIGVNQAHMOII-UHFFFAOYSA-N 0.000 description 2
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 2
- URJHIPLGBLDXIC-UHFFFAOYSA-N 4-amino-N-[2-(methoxymethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=NC(=NC=C1)COC URJHIPLGBLDXIC-UHFFFAOYSA-N 0.000 description 2
- NXYKSXZSDOBSNH-UHFFFAOYSA-N 4-chloro-2,6-bis(methoxymethyl)pyrimidine Chemical compound COCC1=CC(Cl)=NC(COC)=N1 NXYKSXZSDOBSNH-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 230000000973 chemotherapeutic effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- VOGSVUQENSCLHU-UHFFFAOYSA-N 2,6-bis(methoxymethyl)-1h-pyrimidin-4-one Chemical compound COCC1=CC(O)=NC(COC)=N1 VOGSVUQENSCLHU-UHFFFAOYSA-N 0.000 description 1
- GZQNTJUBUHAMCD-UHFFFAOYSA-N 2-(2-methoxyethyl)pyrimidin-4-amine Chemical compound COCCC1=NC=CC(N)=N1 GZQNTJUBUHAMCD-UHFFFAOYSA-N 0.000 description 1
- DWAJCKKINDTXEC-UHFFFAOYSA-N 2-(ethoxymethyl)-4-hydroxy-1h-pyrimidin-6-one Chemical compound CCOCC1=NC(O)=CC(=O)N1 DWAJCKKINDTXEC-UHFFFAOYSA-N 0.000 description 1
- SUYJAOGGIGEQIC-UHFFFAOYSA-N 2-(methoxymethyl)-6-methyl-1h-pyrimidin-4-one Chemical compound COCC1=NC(C)=CC(O)=N1 SUYJAOGGIGEQIC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WPYUCWSMVJJWFI-UHFFFAOYSA-N 2-ethoxyacetonitrile Chemical compound CCOCC#N WPYUCWSMVJJWFI-UHFFFAOYSA-N 0.000 description 1
- UQUIVPXCXXIPML-UHFFFAOYSA-N 2-ethoxyethanimidamide;hydrochloride Chemical class Cl.CCOCC(N)=N UQUIVPXCXXIPML-UHFFFAOYSA-N 0.000 description 1
- QKPVEISEHYYHRH-UHFFFAOYSA-N 2-methoxyacetonitrile Chemical compound COCC#N QKPVEISEHYYHRH-UHFFFAOYSA-N 0.000 description 1
- XMSFMNAYWPDMBJ-UHFFFAOYSA-N 2-methoxyethanimidamide Chemical compound COCC(N)=N XMSFMNAYWPDMBJ-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- PYDUJAPRBBVWSO-UHFFFAOYSA-N 4,6-dichloro-2-(ethoxymethyl)pyrimidine Chemical compound CCOCC1=NC(Cl)=CC(Cl)=N1 PYDUJAPRBBVWSO-UHFFFAOYSA-N 0.000 description 1
- PDAPVUSPOGTKAZ-UHFFFAOYSA-N 4-amino-N-[2-(ethoxymethyl)-6-methoxypyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COCC)OC PDAPVUSPOGTKAZ-UHFFFAOYSA-N 0.000 description 1
- YWQRHJFLDFXWQM-UHFFFAOYSA-N 4-amino-N-[6-(methoxymethyl)-2-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)C)COC YWQRHJFLDFXWQM-UHFFFAOYSA-N 0.000 description 1
- WIIURJFRTWLHJC-UHFFFAOYSA-N 4-amino-N-[6-ethoxy-2-(methoxymethyl)pyrimidin-4-yl]benzenesulfonamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)OCC WIIURJFRTWLHJC-UHFFFAOYSA-N 0.000 description 1
- QWAQJFVZUYMNTP-UHFFFAOYSA-N 4-amino-n-[2-(methoxymethyl)-6-methylpyrimidin-4-yl]benzenesulfonamide Chemical compound COCC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 QWAQJFVZUYMNTP-UHFFFAOYSA-N 0.000 description 1
- PJDDSABKCQXOGC-UHFFFAOYSA-N 4-chloro-6-methoxy-2-(methoxymethyl)pyrimidine Chemical compound COCC1=NC(Cl)=CC(OC)=N1 PJDDSABKCQXOGC-UHFFFAOYSA-N 0.000 description 1
- AVELSBXWALYUPN-UHFFFAOYSA-N 4-hydroxy-2-(methoxymethyl)-1h-pyrimidin-6-one Chemical compound COCC1=NC(O)=CC(O)=N1 AVELSBXWALYUPN-UHFFFAOYSA-N 0.000 description 1
- IKGGFUSHTLTYIT-UHFFFAOYSA-N 4-methoxy-3-oxobutanoic acid Chemical compound COCC(=O)CC(O)=O IKGGFUSHTLTYIT-UHFFFAOYSA-N 0.000 description 1
- TUWLYFAEAPMOJS-UHFFFAOYSA-N 6-(methoxymethyl)-1h-pyrimidin-4-one Chemical compound COCC1=CC(O)=NC=N1 TUWLYFAEAPMOJS-UHFFFAOYSA-N 0.000 description 1
- ZEEJRACEEDQANN-UHFFFAOYSA-N 6-(methoxymethyl)pyrimidin-4-amine Chemical compound COCC1=CC(N)=NC=N1 ZEEJRACEEDQANN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- KYEBOOPUUWAYBK-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)C Chemical compound C(C)(=O)NC1=CC=C(C=C1)S(=O)(=O)NC1=CC(=NC(=N1)COC)C KYEBOOPUUWAYBK-UHFFFAOYSA-N 0.000 description 1
- YBGAMOJCPBPKTJ-UHFFFAOYSA-N COCC1=NC(COC)=NC(NS(C(C=C2)=CC=C2N)(=O)=O)=C1 Chemical compound COCC1=NC(COC)=NC(NS(C(C=C2)=CC=C2N)(=O)=O)=C1 YBGAMOJCPBPKTJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- XPOLVIIHTDKJRY-UHFFFAOYSA-N acetic acid;methanimidamide Chemical compound NC=N.CC(O)=O XPOLVIIHTDKJRY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- JVXZJEUVAOVXIX-UHFFFAOYSA-N propan-2-one;pyridine Chemical compound CC(C)=O.C1=CC=NC=C1 JVXZJEUVAOVXIX-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MGWMPVXITSXYNK-UHFFFAOYSA-N sodium;n-(4-sulfamoylphenyl)acetamide Chemical compound [Na].CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 MGWMPVXITSXYNK-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1473462A CH441364A (de) | 1962-12-14 | 1962-12-14 | Verfahren zur Herstellung neuer Sulfonamide |
| CH244763 | 1963-02-26 | ||
| CH1313463 | 1963-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115842B true NO115842B (enrdf_load_html_response) | 1968-12-16 |
Family
ID=27173721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15123363A NO115842B (enrdf_load_html_response) | 1962-12-14 | 1963-12-13 |
Country Status (8)
| Country | Link |
|---|---|
| DE (2) | DE1248055B (enrdf_load_html_response) |
| DK (3) | DK116284B (enrdf_load_html_response) |
| ES (1) | ES294470A1 (enrdf_load_html_response) |
| FI (1) | FI43991B (enrdf_load_html_response) |
| FR (1) | FR3731M (enrdf_load_html_response) |
| GB (2) | GB1035917A (enrdf_load_html_response) |
| NO (1) | NO115842B (enrdf_load_html_response) |
| SE (2) | SE311654B (enrdf_load_html_response) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB886693A (en) * | 1959-03-04 | 1962-01-10 | Ici Ltd | Heterocyclic compounds |
-
1963
- 1963-12-10 DK DK574463A patent/DK116284B/da unknown
- 1963-12-10 DE DE1963C0031632 patent/DE1248055B/de active Pending
- 1963-12-10 DE DE19631445607 patent/DE1445607A1/de active Pending
- 1963-12-13 NO NO15123363A patent/NO115842B/no unknown
- 1963-12-13 FI FI246363A patent/FI43991B/fi active
- 1963-12-13 ES ES294470A patent/ES294470A1/es not_active Expired
- 1963-12-13 SE SE1392663A patent/SE311654B/xx unknown
- 1963-12-16 GB GB4964163A patent/GB1035917A/en not_active Expired
- 1963-12-16 GB GB49640/63A patent/GB1021395A/en not_active Expired
-
1964
- 1964-03-06 FR FR966452A patent/FR3731M/fr not_active Expired
-
1965
- 1965-05-07 DK DK231865A patent/DK115550B/da unknown
- 1965-05-07 DK DK231765A patent/DK117634B/da unknown
-
1966
- 1966-12-28 SE SE17797/66A patent/SE321476B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1035917A (en) | 1966-07-13 |
| DK116284B (da) | 1969-12-29 |
| DE1445607A1 (de) | 1968-12-05 |
| SE321476B (enrdf_load_html_response) | 1970-03-09 |
| SE311654B (enrdf_load_html_response) | 1969-06-23 |
| ES294470A1 (es) | 1964-06-01 |
| GB1021395A (en) | 1966-03-02 |
| FR3731M (fr) | 1965-12-06 |
| DK117634B (da) | 1970-05-19 |
| FI43991B (enrdf_load_html_response) | 1971-04-30 |
| DK115550B (da) | 1969-10-20 |
| DE1248055B (de) | 1967-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2430439A (en) | Sulfonamido pyrimidines | |
| US4323570A (en) | Substituted aminopyrimidines | |
| CA2634676C (en) | Trisubstituted amine compounds as inhibitors of cholesteryl ester transfer protein cetp | |
| NO115741B (enrdf_load_html_response) | ||
| JPS6354714B2 (enrdf_load_html_response) | ||
| CA1110623A (en) | 2-substituted 5-hydroxy-1h-imidazole-4-carboxamide derivatives and their preparation and use | |
| WO2002012199A1 (en) | Heterocyclic mutilin esters and their use as antibacterials | |
| EP0056319B1 (en) | Substituted pyrimidin-2-ones and the salts thereof | |
| US3249603A (en) | Novel pyrimidine sulfanilamides and processes for their preparation | |
| US3361749A (en) | Certain n-pyrimidyl anthranilic acid derivatives | |
| US4329460A (en) | Uracil derivatives and production thereof | |
| NO115842B (enrdf_load_html_response) | ||
| US3432493A (en) | Substituted sulfanilamides | |
| US3328395A (en) | 6-halo-2-amino substituted-4-sulfanilamido-pyrimidine compounds | |
| NO141137B (no) | Apparat for avlesning av en plateformet opptegningsbaerer | |
| US4255574A (en) | Process for preparing 2,4-diamino-pyrimidines | |
| US3317536A (en) | 4-benzenesulfonamido-pyrimidine derivatives | |
| US2488081A (en) | Production of 2(para-aminobenzenesulfonamido)-4-methylpyrimidine | |
| US3277093A (en) | (optionally-2-substituted) 4-halophenyl-5, 7-diketo-6-alkylthiazolo[4, 5-d]pyrimidines | |
| JPH06100540A (ja) | ５−イソキノリンスルホン酸アミド誘導体 | |
| US2650922A (en) | Disubstituxed derivatives of g-amino | |
| US3091610A (en) | Sulfa compounds and processes | |
| US3505331A (en) | Process for preparing 2,4-diamino-7-chloropyrido(2,3-d)pyrimidines | |
| US2827457A (en) | department of commerce | |
| US2980678A (en) | Pyrimidines |